Drew, My 1950s Mentor Drew
By Miss Wendi Robertson, a Senior Citizen Transvestite
Drew was the adult son from the first marriage of my "Aunt" Etta (a close friend of my grandmother). Drew was a bachelor, and a career Navy warrant officer. When he retired after 20 years of service, he became a night clerk at a hotel.
When I was age 12, both Drew and his mother visited our family and spent the night. Due to a shortage of beds, my parents told me that Drew would sleep with me. This was fine with me because I had always liked Drew. At this time, Drew was in his mid- forties.
During the night I awoke to Drew fondling my penis! I told him to stop it, and he did. Perhaps an hour later I awoke again to the same thing. This occurred 4 or 5 times during the night. What message did I send him by not leaving the bed the first time he molested me? At age 12 I was not sophisticated enough to figure that one out. In fact, I had only masturbated a few times so sexuality was just emerging for me.
Drew also cuddled close to me and I could feel his penis against my ass through my pajamas. I moved away from him but he did this again and again. It didn't make much sense to me at the time.
Just about a year later I had my first cross-dressing experience when I donned my sister's sexy one-piece Catalina swimsuit and then masturbated to a most intense orgasm. About a year after that, at age 14, it occurred to me that I would like to share Drew's bed with him, but with me in a girl's sexy swimsuit! I didn't know what to expect, but I had concluded that Drew was a homosexual and I wanted to be his homosexual student. I didn't know whether I was a homosexual, because I really like girls a lot. Yet, I felt a great lust in my loins to be with Drew once again and this time say "yes!" instead of "stop it!"
I found out from mom that he lived with Aunt Etta within a bicycle ride of our home. I stopped by on the pretense of visiting Aunt Etta. They were both at home. Finally, she left the room and I told him quietly that I wanted to speak privately with him. He seemed to beam and said, "Sure, Buddy, let's go for a walk."
We walked for a while, engaging in awkward small talk. We arrived at the park and set on a bench where no one else was nearby. He smiled at me, looked me directly in the eye, and said, "Buddy, are you thinking about our night together two years ago?"
I hung my head and softly replied, "Yes, Drew, very much so."
"Go on," he said, with kindness and interest in his voice.
"Drew, I want to go to bed with you again. I am ready to learn from you.I am ready to be your girlfriend."
He smiled and said, "I suspected you liked what I did that night, but that you just didn't know yourself yet."
I said, "So it seems.so it seems. I am embarrassed but I have to tell you something."
"What is that Buddy?" he asked with kind inquisitiveness.
"I like to wear my sister's swimsuit or panties and masturbate," I replied. I added, "I want to be in bed with you while I wear a sexy girl's Catalina swimsuit."
He took my hand in his, gently squeezed it, and said, "Oh Buddy, I would absolutely love to be with you like that!" He then placed my hand on his crotch and I could feel his rock hard penis! My penis was rock hard, too! I now knew that I excited him and he excited me; there was no stopping this mutual interest and desire from becoming an intimate affair!
Drew said, "Can you come to my hotel next Saturday morning at 8:00 AM with the swimsuit?"
I said, "I would like that. Will you have a room for us to use?"
"Absolutely, my dear," he replied, "And you will become my teenage girlfriend and you will love being a girl for me, my darling Buddy boy."
I thought, "I hate my childhood nickname but `Buddy Boy' has such an erotic sissy-boy ring to it!"
I went home and couldn't think of anything else. I finally went to the bathroom and jacked off into the toilet thinking of Drew and me as queer lovers. When I ejaculated into the toilet, I softly cried out, "Oh fuck, I want so to be a teen girl.my darling Drew's teen girl friend!" I thought of Drew jacking off at the same time, thinking about me as his girlish sissy boy!
The week passed so slowly. I masturbated three or four times a day thinking of becoming a sissy queer in Drew's masterful arms. I thought constantly of having felt his rock hard penis through his pants in the park. I felt like I was about to become a whore of sorts, and that excited me to no end!
Saturday finally arrived! I showed up at Drew's hotel at exactly 8 AM with my sister's Catalina swim suit in a brown paper bag. Drew beamed when he saw me. He softly said, "Wait here five minutes then come to room 224."
I waited then went to the room and softly knocked on the door. Drew let me in and he was wearing purple silk pajamas. He closed the door and took me in his arms and kissed me! I melted in his arms. My dick got hard immediately.
He sat me down and showed me a makeup kit he had brought with him. He applied lipstick to my pouting lips, rouge to my cheeks, and eye shadow and liner around my eyes. He placed a pearl necklace around my neck and a wedding ring on my left hand! He then placed clip-on earrings on my ears and had me don thigh-high nylon stockings. I looked in the mirror and saw my made up face with my boy's haircut. I looked utterly cute and oh so queer! I loved what I saw and the girlish emotions I felt.
I took off my clothes and felt both intense excitement and embarrassment at the same time. As I took off my underwear my penis stood rigidly at attention. Drew put his arm around me and said, "Take down my pajama bottoms, baby." I did and gasped when I saw his very hard penis. It was much larger than mine. He placed his penis next to mine and said, "Mine is average size, Buddy, so you can see you are quite small."
I winched a bit and said, "Is that a bad thing, Drew?"
He replied, "Oh, no, Buddy, it's wonderful for a sissy to have a small dick!"
I took the swimsuit of the bag and handed it to him. He started feeling me up from my legs to my buttocks, and he gently cupped my balls and cock. He then helped me into the swimsuit and instructed me, "Place your dickie flat up against your tummy, my hot Buddy Girl." I did as Drew instructed me, and worked my very hard little dick until it was flat up against my tummy, constrained by my girl's swimsuit. I felt like a high school nymph with my vaginal mound showing. And, that is how Drew saw it, too.
He then said, "Oh, Buddy, you are so cute and femmie. Your vaginal mound is quite apparent my sissy, darling wife and your sissy sex obviously needs attending to by your new husband!" He felt me there and said, "Oh, yes, my girl is all excited! I felt like I was going to have a spontaneous ejaculation when he called us husband and wife!
He gently forced me down onto the bed and began to lightly rub the length of my erection through the sexy material of my swimsuit. He softly said, "Baby, I am rubbing your clit!"
I moaned and said, "Oh Drew, darling, that feels so good!" He then began to passionately French kiss me and I accepted his tongue into my mouth like it was his cock into my vagina! I could taste my lipstick and I know he could too.
He then reached over to a jar of Vaseline I hadn't noticed before. He lubed his index finger with a lot of the goo then forced the leg of my swimsuit aside and he entered my ass with his greasy finger! Then, he started to finger fuck me! With his other hand he rubbed my "vaginal mound" lightly but rapidly. Drew was exactly the lover I had been longing for the past year, or so. I felt so queer, so feminine, and so submissive.
He said, "Lie on your tummy baby and get ready to become a real woman!" I was so excited and did as I was told. He lies atop me and begin to rub his cock against my ass as he reached in the top of my swimsuit and lightly rubbed my nipples. I cried and whimpered, "Oh my darling man, fuck me!" With lust in his voice, he said, "Beg for it sissy, beg me to fuck you!"
I loved this so much! I said, "Oh darling master, please fuck your swimsuit sissy slut!"
I could feel the head of Drew's rigid cock pressing against my now well-lubed homosexual vagina. Yes, my ass was my boy pussy! I knew this is what I needed so very much, just like the real girls need! I whimpered, "Oh darling Drew, take me!" His cock slowly slid into me until we was fully inside me. I could feel his balls resting against my balls.
He slowly made small thrusts and said, "Oh fuck Buddy Boy, your sissy boy pussy feels so fucking good! You are my tight boy fuck.my boy fuck who wants to be a girl!"
"Yes!" I replied, "Fuck me, sir, and make me your sissy!"
Drew reached under my groin and began to rub my little dick through the material of my swimsuit. I felt close to a jack off climax. At the same time he started to fuck me good and hard. The sound of his groin slapping my ass as his cock took my boy pussy was simply wonderful! He was grunting now, breathing hard, and calling me names, "My fuck slut, my cunt boy, my bitch..take my hard cock! Here I come Buddy Boy, here I come!" With this he gave me those tale-tale short strokes until he cried out, "Oh fuck! Fuck yes! Ahh! Take my cum my sweet slut boy!" As I felt his ejaculate fill my ass I shot a huge load of sissy-boy cum into the crotch of my sexy swimsuit.
I was in love with Drew and wanted to go steady with him as his sissy boy girlfriend! We became homosexual lovers until I graduated from high school. Over those few short years, he bought me an extensive wardrobe and several wigs and taught me makeup and how to dress and act like a woman. He also taught me how to suck his cock as well as taking his hard cock in my sissy- boy's ass pussy.
Drew especially loved me in girdles of all types. Girdles were so in vogue in those days. I shared Drew's love of girdles. We both especially liked me in an open-bottom girdle with garters and real nylon stockings. A satin bra was always a must. Sometimes I wore panty girdles with garters and Drew would make love to me like our first time, through one of the panty legs. Drew loved me in skirts and satin blouses, of which we had many. I also had many very feminine full slips that I wore beneath my skirts and satin blouses.
Although I never appeared in public dressed (so forbidden in those days) I would ride around in his car at night with him when I was fully dressed. We would often drive to the mountains and fuck in the car like heterosexual couples did a lot in those days.
One time I asked Drew, "Honey, since you enjoy me the most when I am fully cross-dressed why didn't you end up with a real woman?"
He held me, hugged me, felt up and down my nylon-clad legs and softly replied, "Because women don't sexually excite me, men do. But, what excites me most of all is a teen boy in women's clothes; a teen boy who obviously loves pretending to be a sexual female! The key, though, Buddy Girl darling, is that it is a pretense, because you are indeed a male, albeit, a very exciting male because you are so submissive and feminine."
I swooned and melted in my homosexual "husband's strong arms. I felt so good about my homosexuality and cross-dressing because of his nurturing and love.
Note:
This story is a true autobiography as to the first (only) encounter with Drew. The part about my first cross-dressing experience in my sister's one-piece Catalina swimsuit is also true. The remainder is fiction, although during the period 1957-60 I did wear much of what I describe in the latter part of the story, but alone and in my "closet."
Those with similar interests or memories (especially seniors who were teens in the 1950s) please feel free to contact me at: wendi@wendirobertson.net.